Until you're no longer in sorrow
by Houki Minami
Summary: [POST VOLUME 21]/ It has been a month since the Demon Lords and their affiliate sealed themselves with 666 in order to save the world, and Grayfia is the one who has been hit the worst for the loss of her dear Sirzechs. Hyoudou Issei apply himself to try to cheer her up, but things suddenly take an unexpected turn./ Grayfia X Issei SMUT, Netori(?)
1. Until you're no longer in sorrow

**Hey, how is it going, fandom? If you've read the lastest volume of DxD, the 21 one, maybe you're excited as me. Seriously, whatever happened there was sick, both ways, and everything that I was expecting to happen when 666 was finally out of it's cage... Kinda happened. Civil war and stuff, people losing members and Issei and Vali getting power-ups and stuff. Unfortunately, my dear dear Zechs didn't make it... Kinda, he and his buddies pulled a 'sonic '06 blaze' and poor Grayfia, was left behind with their son. That's sad...**

 **How do I coup with that? By writing a smut, of course. Vali had his happiness back in 'Daddy Vali', now is Issei turn before I shift my attention back to butt-buddies.**

 **Before when begin, a little warning: This might be considered a NTR fanfic since Sirzechs isn't really dead, and it's maybe kinda OOC due to circunstances... But my ever excuse for it, this is the DxD fanon, nobody cares about canon. With that being said, have a nice read and... Oh, sirzechs, why? You were the demon lord, the sexta espada, a space cowboy, a heroic spirit and older brother of the two most adored singers in otaku culture. Why do you have to leave us?**

 **As always, DxD doesn't belong to me.**

* * *

"G-Grayfia-san, we shouldn't be doing this..."

"Mooh~ Issei-sama, I've already said you can call me 'Ane' when we're alone like that." Echoed inside the Gremory's bath house, where a certain couple was enjoying the company of each other, although it could only be said by one side, really.

Hyoudou issei, Rias Gremory's precious pawn and host of the Welsh Dragon Ddraig and his Sacred Gear Boosted Gear, was sitting on the floor and trying his hardest to hide the hard-on he was having by staring at the nude figure of Grayfia Lucifuge, the descendant of the Lucifuge clan and Sirzechs Lucifer's wife(widow?), who was now on her fours and reaching her hand to the elevation on Issei's censoring towel, her face burning in bright red indicating she has been drinking a few again, much for the Sekiryuutei's horror. The reason for this shock, however, was beyond the simple slapstick he has to deal with everyday in his typical romantic comedy everyday life...

It has been almost a month since the reseal of 666(Trihexa) in a different dimension, thanks to the sacrifice of the brave leaders of the Three Factions and their affiliates in order to hold the apocalyptical beast, and despite only Ajuka Beelzebub now on command of the underworld, things are at least coming back to normal at a slow but steady pace, and even Issei was now cured from his Oppai-allergy...

But the same couldn't be said about the Lucifer's widow. Inside her circle, the so-called Gremory maid would be composite, calm, stoic and her typical self, but according to Rias, Grayfia would literally crash once there wasn't anyone looking, mourning for her beloved Sirzechs, and turn a lot more emotional when facing Millicas, breaking the poor boy's heart. Issei couldn't completely, but he understood such grief, after all, he was his onii-san, his Beloved Rias' older brother, the great Satan and probably the nicest person he ever knew. To think he would end up like that... But Grayfia-san was also suffering for that, in a scale the Sekiryuutei couldn't imagine. The silverette would turn progressively sicker and sadder, and even with her own grief, Rias couldn't handle her sister-in-law like that. Hyoudou Issei, being still the perverted but kind goofball, decided to give it a try and cheer the Ultimate Queen up and, knowing his own talents to deal with people like that and his loyalty towards her, Rias allowed him to do as such, confident that he would do just that...

Unfortunately, things turned for the worst for Issei and now, he was cornered by the ultimate queen in the bathing center, completely drunk, whose hands were reaching his hidden erection while her ungodly body was giving him all the reasons to react like that...

"Huuuh~, boys these days, so healthy and lively." The drunk queen said with a smile, reaching for Issei's erection. The pawn, divided between his own lewdness and the honor for his onii-san, could only crawl away from the lustful yet confused glare from his future sister-in-law, when unfortunately he hit a wall, and was now cornered by the Queen, just like a mouse by the eyes of a cat.

"Grayfia-san, we really shouldn't be doing th-...!" The rest his sentence turned into a weak, hoarse moan when the silverette finally caught his throbbing rod by the outside of the towel, holding the erection down with her fingers while the thumb was massaging the tip as gentle as it could. Even with the cloth blocking the raw touch, Issei could feel how soft her hand was. The queen then proceeded to move her hand up and down, gently stroking Issei with all the care to not accidentally harming it with the towel. With that, the Sekiryuutei groaned even louder. This was completely different than doing it by himself! "G-Grayfia-san...!"

"It feels good, right issei-sama? I'm glad that my services are making you happy." She said in her now groggy tone, Issei being too stunned to do anything besides moan. The silver queen licked her lips, that boy was so charming with this struggle of his, between his own lust and love for both the Gremory siblings. He gasped when she went ahead and cupped his jewels from under the cloth, massaging both his most sensitive parts, making sure her soft hands were touching the right spot and in the right rhythm. By the sounds he was doing, she was doing the right thing. "Does it feel good, Issei-sama~? Can you feel it~? My hands, touching you just right..."

"G-Grayfia-san..." The poor Sekiryuutei could only mutter her name. This is wrong, this whole situation is wrong, and he knows that very well. Yet, he can't deny the fact it feels good. The queen reached under his towel and was now stroking him rawly, the thermic shock between her naturally cold and slender fingers and his hot, throbbing erection made him groan even louder, trembling to the last string of hair on him and feeling the build-up on the tip of his manhood scale to unbearable levels. He was ready to blow. "Stop, Grayfia-san...! I-I'll blow...!"

"You're going to come, right? Go ahead and blow your load, Issei-sama~! Please~!" She said with her hands now gripping tightly on him, the throbbing member getting hotter and hotter while not escaping her grasp. Her hand was already slippery and sticky thanks to the pre-cum that was coming from the tip, and every time she massaged his shaft all the way from the head to his crotch, indecent noises would come out, a few drops flying around indicating how fast and wild she was servicing him.

"Aaah~... Aaah~... Grayfia-san...!" And Issei couldn't hold it anymore. Still fighting his own libido to the very end and tightly gripping his own hand, he reached the peak of his own pleasure, letting his nectar flow through his rod and blow, sprawling all over under the towel and in Grayfia's hand. There was so much coming from such young boy, the drunk maid could only hum in amazement, feeling the flow of his seed with her own hands, throbbing uncontrollably with the Sekiryuutei moaning in a mix of regret and pleasure every time he would blow a new one. In the end, Hyoudou Issei was reduce to a panting mess, sweat running down his forehead and chest while the relieved feeling and cold wind would take his whole body off-guard, but the grip around him finally vanishing. "Haaaah~... Haaaah~... Rias... Onii-san..."

"So much to give... Sure is a young boy with a lot of energy..." In a totally different world, the grey-haired beauty was looking amazed the aftermath/result her little service on the Sekiryuutei left. Her love nectar was thick, sticky, and smells so bad, not to mention the amount it came. Huh, no matter how many pretty girls are around him, the boy apparently can't have his time alone, nor have a time alone with anyone, poor thing. It'd be both unclean and wasteful to let her hands be like that, at least according to her groggy mind, so Grayfia stuck her tongue out to lick the semen off her hands. It was salty, smelly, but made her body feel somehow hot. She gargled it a little inside her mouth before swallowing it whole. Truly, Issei-sama was indeed a hero to let himself reach this point. Even now he was doing his best to avoid looking at her body, yet failing at that if his new erection was anything to go by. Grayfia smiled, and again reached for that volume under the towel which has been stained by his love juices. "A lot of energy, indeed..."

"Wait, Grayfia-sa-..." And again he was cut by another have of pleasure when she began stroking him by above the towel. He was already kinda groggy from the previous orgasm, and was now quite sensitive down there. He might have an erection, but Issei was still catching up with his own tempo. A second of lucidity, and the Sekiryuutei gulped hard, pulling some strings and winning over the lust his body was feeling to muster the words. "G-Grayfia-san, why are you doing this? If it's because of Onii-sa-...!"

"Shhhh~..." But he was again interrupted by the silverette, who slid her wet, soft and hot body all over his muscled and toned one and silenced him with a finger on his lips. Not only for that, Issei stopped when he felt her ungodly breasts touch his bare skin, her hard nipples massaging around his chest, giving him both a pleasuring and tickling feeling. He was forced to look at her again when a hand reached for his hair and pull closer to her face. He can smell the alcohol coming from her mouth. "Just relax, Issei-sama~. You've been fighting this whole time, and never had the release you wanted for so long~. I'm just doing the best for my beloved Future brother-in-law, so let me service a little and help you as a maid from the Gremory house~."

"But Grayfia-san is also feeling down, aren't you? Rias told me what has been happening to you, and I, as well as everyone else, am worried about you." Still not letting go of his sanity and trying to pull the string back, Issei said while still with his eyes locked against her silver stare. All he received was a surprised gaze, but then a quite saddened look. Maybe it's working, maybe now he can escape this... Dream with consequences and cheer her up! "Look, everyone is sad about what happened, I'm sad for Onii-san too! But...!"

Grayfia has indeed become the epitome of unpredictable: in such situation, when Issei thought he had the upper hand to talk some sense back to her, she kissed him. The Sekiryuutei was too shocked to even react to that, making the silverette take the advantage over him and completely dominate his mouth. The taste of her mouth, the taste of sour grapes and alcohol, plus her own wildness was making the brunette himself drunk with either pleasure or by indirect contact, their bare skins touching each other and her own breasts going up and down on his chest, their nipples touching sending pleasurable electric shock through both their bodies, and cutting the last strings of sanity on the Sekiryuutei's head. In the end, Grayfia parted their lips, a string of saliva separating their tongues and she was still drooling into his mouth, and before he could do or say anything, he felt another shock coming from his nether areas.

"Oh my, so hard in so little time. It's even bigger than before~." Grayfia was again playing with him, using her fingers to massage the tip while delighting herself seeing the blushing hapless expressions the Sekiryuutei would do. Her mind was far away from this world(much more like... No, she won't remember him now, she's now servicing the Sekiryuutei just for that), so she had no problem and kissing him one more time, albeit this time was a light lick on the lips, and trace his whole, from the said kiss to his chin, neck, collarbone, chest, stomach and finally his crotch. Grayfia was now looking at the throbbing volume, struggling under the cloth as now there was no way for her future brother-in-law to hide all he was feeling just now, that being lust and desire. Just by looking and smelling, she could feel herself getting wetter and tingler down there, her thighs also trembling from the amount of sexual tension between the two and compressing her most intimate part so that she could control her own libido without going insane. "It looks so painful, let me help you with this problem, Issei-sama..."

This time Issei couldn't say a thing, her breath was touching him, and the best he could do was to groan at the painful yet pleasuring sensation. He needed a relief for that, otherwise he would explode! Unfortunately for him, the situation on his nether areas became even more frustrating when Grayfia suddenly pulled the towel away for the world to see what it was hiding, his own exposed area being attacked by the wind, making the Sekiryuutei shiver as his rod grew bigger with such petty stimuli. The silverette 'taking care' of him could only smile in drunk amusement.

"What a cute thing, Issei-sama, hiding under the foreskin. Allow me to help you with that~." Again, Grayfia caught him by the shaft, but instead of her hand, she used her lips to 'help' him. Issei groaned loudly and tossed his head upwards with this new sensation, but he could still feel Grayfia's warm, soft mouth pull the foreskin from his tip and wet the rest with saliva while at it. With that done, the maid removed her mouth and flashed a smile seeing the Sekiryuutei exposed holy sword. Now that's where the true fun starts~. "Now then, If I may~..."

The first thing the silverette did was to stuck her tongue out and lick all the way from the base, through the shaft and to the tip, also gaining a moan from the Sekiryuutei, tasting the salty flavor of his pre-cum plus his last orgasm and taking it away from his soft skin. The licked and licked, and eventually his manhood would slip her since it was throbbing so much, touching her cheeks, nose, lips, even the bridge of her eyes, not that she would mind much, by his moans, he was also enjoying touching those parts. In the end, Grayfia cleaned the whole area from his last shots of pleasure, but the tip was still dripping some and ruining her whole job. Fortunately, she knew what to do in this situation...

With one final lick of love, Grayfia then stopped at the tip, and before anything, she gave a light peck at the small hole in there, and an act of both mischief and affection. However, Issei couldn't hold another gasp of pleasure when she suddenly used her tongue again to massage that same hole, slowly reaching her own lips for the tip. Finally, she again kissed him, and let him slide to inside her mouth, her soft lips gently letting him in while her tongue was now massaging the rest of it from also inside.

That moist, warm and new type of cavity was too much for Issei to handle in his virgin existence, and then he again blew his load inside Grayfia, who was caught by surprise for the shots of love inside herself, the sensation on her mouth being assaulted by continuous loads of semen while lips were feeling all of them come from through his shaft to shot at her again. In the end, her mouth was dripping of his seed, filled to the brink since she had no time to react properly, and falling in her cleavage. The scare died off, and she could only moan to that warm, sticky substance inside her mouth. She finally let go of herself and only now noticed that, in that moment she was assaulted so suddenly, she reached also her own climax, since the dripping in her nether areas wouldn't stop. The glee hit her so hard and suddenly, she didn't even feel touching herself with a free hand. Oh, this is turning way better than she anticipated...

"A-Ah... Grayfia-san, I'm sorry..." Was all Issei could say now that he could look back at her, seeing how helpless she was in such situation. However, the ultimate queen just snapped back from her own reverie, and loaoked at him with teary, but blissful bedroom eyes. Grayfia licked around the brink of her lips and removed the dragon in it, still filled with love and nectar, which them she proceeded to gargle and finally swallow. He was still so hard.

"Mooh, Issei-sama, I've already said that you can call me 'ane'." She said with a smile, passing her slender finger across her breasts to pick the remaining seed on it and chew on it again. Such sight made Issei even harder, and even with his attempt to hide It again, Grayfia was still fast enough to catch him on spot. She stroked him a few times, and licked the remains that came after, then proceeding to kiss the tip and from there suck the rest stored still inside the shaft. In that meantime, the Issei was on the brink of lustful breakdown, his mind melting from such unfold pleasure. "Now then, shall we try again?"

"Y-Yeah, okay..." He said absent-minded, since there was no way for her to stop, he decided to let himself go a little and then figure things out later, he was really getting out of options and the situation was preventing him to think straight. Such response brought a happy smile on her tired face, and so she nodded and again tried her little act of fellatio. Grayfia swept some of her bangs away from her face, and again wide opened her mouth stuck her tongue out, slow but steadily letting his member slide all the way into her mouth. Issei trembled with it, his now groggy mind intensifying the sensation of first her lips, then the massage of her tongue and teeth on him, sliding all the way until it wasn't visible anymore, all the way inside her moist, warm, trembling oral cavity. The silverette, on the other hand, was on tears now, such big and large thing inside her little mouth, poking her throat, her jaw was already hurting, and his throbbing making her head spin a little. She moaned and tried to not choke on him, making Issei turn back to her. "Grayfia-san, are you alright? Y-You can stop if you want..."

Grayfia however looked back at him and hummed a negative hum, slowly moving away from him, the warm meat and tongue of her mouth working out his shaft, only stop midway and then moving forward again to swallow his rod whole. She proceeded to repeat that same movement over and over again, her head going forward and backwards, saliva and pre-cum spreading all over Issei's member as both lost themselves to lust, Grayfia feeling a sick pleasure in being choked by such strong, big and large thing as her throat was being raped mercilessly and her only ways of communication were reduced to simple gasps her lungs would produce everything her air passages were obstructed. The Sekiryuutei himself reached cloud nine faster: he never thought a blowjob would feel this amazing, and even if he couldn't see her in the act since he shot him head upwards for the sheer ecstasy, he could still hear the lewd noises of moist flesh on flesh and feel his tip reach down the deepest of her system while her meaty muscles and tongue would take care of the rest.

There he is, getting hotter and throbbing like crazy like before, moaning her name with such intensity and trembling up to the last string of hair. He was cumming again, she could feel it just by his reactions. Instead of preparing herself, however, Grayfia went the deepest she could and swallowed him whole again, something hot and large poking her throat and locking the rest of it with her inner cheeks, tongue and mouth muscles. This surprised the red dragon, as he tried to get her off of him before it was too late, but it was no use: the ultimate queen was willing to swallow all of his cum for some reason.

He tried to fight, but it was too late: in another groan he saved up to this point, he shot the salty nectar, as Grayfia's mouth tried it's hardest to milk everything from his sturdy rod, sucking everything down her throat and with her lips doing minimal swallowing moves to force the rest in the base of his member to flow through it and reach her mouth, reaching her own bliss and cumming with every shot Issei would do down her nasty throat. In the end, Issei could only hear the sound of something being gulped down, and then, freedom, the boundaries around his little friend finally being released. With a sigh, he again looked down only to see a drunk blushing Grayfia-san sucking him like a straw, finally letting him go to look at him back, opening her mouth to show all of that sticky, smelly nectar dripping from her tongue, before finally swallowing down her system, with her humming a happy yet slow tune.

"How was it, Issei-sama? Are you satisfied~?" She hummed, smiling yet losing control over the itch in her nether areas. Her head became a even messier chaos, and soon or later, she would either welcome the dragon inside of her, or go insane for it. She needed to keep going with this, because no matter what, the memory of him would come back every time no matter how many orgasms or moments of total disconnection of this world she would have. And if it wasn't drinks or work, it would be sex what will save her from this nightmare. Touching herself was just a temporary solution as she found out, and knowing the Sekiryuutei was a grade-A perverted virgin, he truly wouldn't lose such opportunity. "Or... Maybe you want us t-..."

"Grayfia-san..."

"Huh...?" Now it was her time to be surprised: out of the sudden, Hyoudou Issei tackled her to the ground, and pinned her down, her arms wide open in order to fully exposed her nude and glorious bosom, her fully formed, mature body and pretty face. Has he finally lose it to his own desires? Has his inner temptations and urges take over his better judgement? Truly, she was surprised at first, but a small smile formed in her lips, and she sighed in relief, closing her eyes and letting herself to limp like a doll at his will. Maybe this time... She could finally lost herself and forget about him, even if it's just for a second...

Yes, she would finally have some peace...

"Grayfia-san... I know you miss Onii-san..." However, instead of a savage attack from the hormone-filled dragon, a calm and composited voice called her out, making her open her eyes in surprise and look at the expression the Sekiryuutei was making. He was... Sad, he was expressing sadness. This confused the ultimate queen to no end. She knows him very well; yet he has all the liberties to do whatever he wants with her body, yet did none of them. Instead, he said something that weighted in her heart again. "You miss Onii-san... Don't you? I miss him too, everybody does. But... We're also worried about you! Please, Don't do this to yourself!"

"I... I..." Her vision began to lose focus, as her own mind would become clear again. Yes, she misses her dear, beloved Sirzechs, so so much. She couldn't coup the feeling of losing him, and so she tried to find ways to forget about him; even if it was for a few seconds. And now look where what it led her to: trying to have sex with his future brother-in-law. Such disgrace, she was better than that. She reached her hands for her face to dry the neverending tears. "Issei-sama... I... I... I can't stand living without him... I loved him so much... I just... I just want to forget about him, even for a second..."

"But you don't have to forget about onii-San! You need t-...!" And this was indeed getting old: Grayfia again cut him short as she used her legs to draw him closer and the sudden movement made Issei lose balance and land on her, and her newly free hands touched his cheeks, forcing him to look back at her. Now he was forced to see her own melancholic expression, the endless flow of salty water on her pretty face. "Grayfia-san..."

"Please, just this once..." She asked, touching now foreheads with him, and so lovely gripping her leglock around his waist tighter. "If I continue to think about him like that, I'll go mad. Issei-sama, if you want to help me... Just this once... Make me forget about him, just this time."

"..." Her case was indeed worse than he anticipated. He underestimated her situation, and look where it led him to. He cursed himself under his breath, but his priority now was Grayfia Lucifuge. He came to a single conclusion, and it was the one he was indeed fearful about: he would have to make her forget about Sirzechs, so that they could start her recovery anew. It was the only way. He bit his lips a bit, and then murmured: "Okay. Here I go, Grayfia-san..."

The smile she gave him was at the same time relieving and melancholic, saying at the same time 'thank you' and 'please forgive me' wordlessly. Issei gulped his last drop of regret and then, mentally apologizing to his girlfriend, he came closer and placed a kiss on Grayfia's lips. Those last times were wild and sudden, so only now he could notice about the taste of her mouth: there was something more than just alcohol and sour grapes, there was also something salty. It was her tears, she was still crying. How much grief she has been holding this whole time?

The kiss deepened at a slow pace now, and little by little, Issei started to lick her lips, and then suck on her own tongue, their mouths vibrating every time Grayfia would moan inside his own in pure pleasure. So much toxins, so much glee, she lost herself again in the sea of sensations, and just by touching his tongue she could feel her orgasm coming. Before she could r reach it, though, the red dragon broke their link apart to them trace his saliva down her chi and neck, pecking some kisses here and there down her collarbone to then stop in front of her breasts.

Big, soft, perfectly-shaped breasts, as expected from the widow of the Lucifer demon lord. Not even Rias or Akeno-san were able to let him stay this close to theirs. From there, the Sekiryuutei lost it, and the first thing he did was to take a bite out of her nipple, making the silverette jump from the sudden shock and assault. Issei was now sucking that bosom with all of his mouth, biting her areolae and licking the tip in total bliss. He loves them so much, and to be this close and intimate like that... There's no way for him to lose that opportunity.

"Fwaah~... Issei-sama~... Hyaaah~... Fwaaaah~...!" Was all Grayfia could muster with her breasts being toyed. Her body was now more sensitive than ever, so much even Issei's plays were driving her home. Her wandering hands grabbed him by the hair and moved him closer to her chest, her legs also pulling him in to rub his growing erection in her nether areas. What was hot inside of her turned now into pure lava, and once the dragon pulled with his teeth her pink tip, she couldn't hold it anymore, and came again.

So much sweat, so much smell, wet skin rubbing again skin, their bodies sticky and smelly due to their own climaxes were making Grayfia lose it. His hands would poke, pinch, massage and press her enormous bosom, and once in a while, he would kiss, lick, suck and bite, leaving marks and bruises all over her. For every action and stimuli, she would come a little, her mind going blanker and blanker with each caress, and when the dragon pressed both of her mounds together to suck her nipples at the same time, she completely lost it...

"Aaah~! Issei-sama~!" She said finally letting herself go, spasming her every muscle and tossing her head upwards to give herself to that orgasm. In the end, the only thing left was a trembling, twitchy mess under Issei. She was tired, hurt, out of breath, but the memory of him was not gone. Curses, curses her love for him. There was no other way: "issei-sama, please... Fuck me!"

"Grayfia-san...?" Her choice of words sure was a surprise for him. Not even when in this drunk state, the stoic, composite Grayfia Lucifuge would resort to such crude language, but maybe there wasn't any other way to express her feelings now, and he would be damn if that wasn't a turn-on in any way. She was hiccuping while saying it, however...

"Please, I beg you, Issei-sama~. I can't hold myself any longer~, if you don't fuck me, I'll go mad~! I want your **** now~!" She said in a tone that the dragon could only describe as a mix between a scream of desire and a pitiful plea for help. Grayfia was shameless enough to open her legs and use her fingers to spread her lower lips, exposing her most intimate, sacred part, for him and him alone, which was pulsating like crazy, so lonely and desperate for a friend. Issei bit him lower lip, and his rod hardened instantly, which was now touching her thighs. "Please, I know you love Rias, but just this once... Just this once, take me~! Fill my pussy with your rod and take me~!"

And for that moment, Issei's world suddenly stopped. It just stopped. In front of him, a naked, broken and desperate Grayfia offering herself to him, wanting to forget her sealed husband, the demon lord, and going as far as having sex with her own future brother-in-law to achieve that. His body was saying 'yes', his mind was saying 'yes', and although his heart belonged to Rias and Rias alone, it was also telling him to go ahead and help her, otherwise she would probably descend even more in this spiral of grief and sadness. He set forward, touched her inner thighs and stroked his hard erection against her lips, so far as touching her clitoris and making her again tremble in pain and pleasure. Grayfia could only mutter a 'thank you', and toss her head backwards, closing her eyes, ready to cross the final line and Feel the ultimate bliss. However, Issei was still frozen in place. Grayfia was a beautiful woman, any straight sane man would kill and die to have this kind of service from her, and he was also just a few inches to finally become a man, however...

However...

Onii-san...

"Grayfia... Could you... Turn around, please?" He so shyly asked despite their current situation, taking a deep breath to remove his dragon away from her warm, moist lips and look back at her.

"Huh~...?" The silverette opened her eyes and looked back at him, still sane enough to hummed in confusion, but soon dismissed that and did was he said, laying herself on the cold floor, resting her head on her crossed arms, her hard nipples and soft breasts squishing on the ground, while she supported her lower part on her knees, in a way her butt and pussy were upwards for him to see as bright as day. Such embarrassing position, she would never let herself this vulnerable if she wasn't with Sirzechs or in this kind of drunken situation. She turned her gaze to her behind to look back at the surprised Sekiryuutei. He was so innocent. "L-Like that?"

"Uh... Yeah, like that." He sighed, mesmerized by her glorious ass, that was on par with her breasts(in this situation, he tips his hat to Vali.). Gulping one more time and letting his inhibitions take control over him again so that he wouldn't regret anything midway, he reached for her butt-cheeks and proceeded to give them a light squeeze, making the ultimate queen shiver and moan with his warm hands. Issei then started to massage her warm and soft meaty cheeks, only to spread them and letting them go in a way they'd clash against each other. Grayfia was again at the doors to madness, just the feeling of being watched and exposing herself like that was intoxicating, and she no longer could control the drool out of her mouth and her dripping pussy. In the end, issei stopped his plays, and landed his hands on her hips. She could feel him rub something hot and hard against her read. "Alright, here I go, Grayfia-san..."

"Yes, please Issei-sama..." And then the silverette used one of her hands to again spread her lower lips for him. He was still a virgin, so of course he would have some problems in doing it. She was desperate, but at least her 'older sister' instinct was speaking louder and trying to help him, although she was also doing it for things to go faster. But something happened: instead of aiming for that direction, she felt her butt cheeks again being spread wide to open space, and then something hot poke her not in her pussy, but somewhere completely different. "Ah Issei-sama, wait, t-that's my...!"

Too late. Before she could even finish her sentence, something hot and big violated her rectum in a fast, merciless thrust, spreading and pulsating her tight insides and letting her words die in gasps of surprise, pain and pleasure, her tongue sticking out and her eyes wide in surprise as her lower muscles were still trying to get use to that new intruder. That's right, Hyoudou Issei opted for anally penetrate Grayfia...

"A-Ah...! I-Issei-sama... That's my... That's my...!" Her words again died in her mouth as he removed his rod only to penetrate her again in another dry and fast move. This was completely different from doing the convictional way, and it hurts so much. In the end, Issei resumed his moves inside her ass, every thrust now making her either gasp or moan in a mix of pain and pleasure, his hands now holding her still by the buttcheeks. "A-Aaaaah~... It hurts~... M-My a-... My a-... It feels so~... Ah~...!"

"I'm sorry, Grayfia-san, b-but I can't betray onii-san! S-so I'll use your ass instead~!" He said apologetically, taking his own gasps for air as he could feel his shaft bend a little inside her tight and pulsating ass, gripping him so hard he thought it'll break him there and now. Yes, no matter his intentions or the situation, Issei couldn't ever forget about his onii-San, which would also includes Grayfia's special place. It was Sirzechs' and sirzechs' alone, so his only option to deal her desperation and recovery lied on her ass, and so he did...

Her saliva and his own cum worked wonders as lubes, so his rod was so easily going in and out of her, doing indecent wet noises every time he would enter her meaty insides. Grayfia was now at mercy of Issei's manhood, her sensitivity skyrocketing with that new sensation of violation, making her bit her arm as hard as she could. She felt violated, embarrassed, ashamed, yet she couldn't stop but to think of Issei and only Issei, him remodeling her anus and massaging her rectum as he poured her without mercy, his fingers craving deeply in her ass and holding her into his reaching zone. Now Grayfia had completely subdue to Issei, she was now his whore, and there wasn't anyone in her world besides him anymore. Her pain doubled as lust now, and so was her turn to move, pulling her ass back to his so that he could pierce her deeper. She move, she shook her hips, she buried him deeply into her, tears and drool dripping from her face as she was the reaching for her climax...

"Aaah~...! Issei-sama~...! Issei-sama is pouring his hard **** into my naughty ass~!" She moaned, giving up any kind of logic and reason to lost herself into pleasure, shutting any other function in her brain besides control over her hips. But it didn't stop there: suddenly the dragon buried himself deeply into her and picked her arms to furiously pour her again, riding her wildly as she felt herself flying, her breasts bouncing in the air, suspended by her arms on her back, issei reaching her deepest part! "Aaaaah~...! Aaaaah~...! I cant...! I can't...! Issei-sama... I'll cum... I'll cum with my ass~! **I'll cum with my ass** ~!"

"I'm can't hold myself too... Grayfia-san...!" And in those last moments, both have turned Ito lustful animals, losing any kind of sanity that was left and just letting themselves shock against one another! Such grief, such sadness, such despair, Issei would help her with that here and now, and then deal with it for good, so this wouldn't have to happen ever again!

In one final move, Issei removed his manhood from her recrum only to thrust her deep and hardly as possible again, and then release his inside to even deeper. Grayfia, who was now helpless against anything, could only choke on her own saliva and pleasure feeling her ass being assaulted by something hotter than lava, spreading all over her walls and being squeezed by her own muscles, as in her body was doing it unconsciously for more of Issei's warm nectar.

In the end, both froze in place, the expression on the silverette's face telling how hard Issei had broken her, while himself was controlling his breath, trembling as his sanity and reason would slowly crawl back to his mind. He let go of her, slowly putting her on the ground, and removed his member from her rectum, which proceeded to 'spit' his sperm from it, along with some blood as a result of his own roughness and her anal virginity being broken as well. The ultimate queen was now a messy whore on the floor, her ass still pointing to the heavens, as her insides would continue to spit semen from the previous love-making and mix it with her own juices dripping from her vagina. Her tired, teary and broken face was also sporting a satisfied, relieved smile, and her whole body was twitching and trembling every time she moved, her breasts squishing on the floor and her arms limp. She was tired, she was broken, yet she was happy... Somehow, she was happy...

"This is bad... I shouldn't have done it like that." Issei sighed now completely sane, as he picked the queen and cleaned her up to dive into the hot waters with him. She has fallen asleep during her last moments of bliss, but at least she had a happy expression on herself before passing out, her sleeping figure staying as calm. He sighed in relief, caressing her face and pulling the bangs away from her eyes, just to see how serene she was now. "Grayfia-sa-... Ane, I'm sorry. I'll help you with your grief, so that I won't have to do this with you... Ever again."

Strange words coming from a massive pervert such as himself, and he even laughed a little for that, not to mention he would have a hell a lot to explain once he gets back to the Hyoudou residence. But for now, he'll do his best, after all, she was his onii-san's wife, and he'll help her no matter what. For some reason, the queen came closer and hugged him, still asleep, and so they stayed like that, sharing that moment, in total silence, in seconds that seemed like hours...

Yeah, one day... He'll find a way to help her.

* * *

. **..**

 **...**

 **If you're reading this far, you either hate me or having an awkward moment in your pants, and for that, i'm sorry. A friend of mine always said that, if you don't make readers hate/cry for/be pissed off by your work, you're not a good writer in any regard, including fanfics.**

 **I regret nothing... And everything. I'll dig myself deeper and write something else, but it's up to you readers: Should I write an Kiba X Xenovia fic, a Koneko X Gasper fanfic or a Saji X Ruruka X Momo threesome fanfic? I'll think Yuri fanfics later, thank you. Just kidding.**

 **As always, stay golden.**


	2. Until you're completely hollow

**So, yeah; Hellos from Houki Minami y'all. Since I'm starting quite an arc in DxD:R and honestly life has been catching up with me more than I'd like to, I decided to close the last-chapter's open ending with this little epilogue since I feel like writing something like this now. Hey, Souma finished off like this, my first fanfic, so why not this apparently qute popular Issei x Grayfia? So here it is, although not as much as last chapter, ehehe~! But I'll tell you this: Issei finally made Grayfia happy.**

 **Without further addo, I hope you have a great read!**

 **As always, dxd doesn't belong to me~.**

* * *

"Ise? Ise? Ise!"

"Eh...?" And then he was back. Hyoudou Issei snapped back from his small reverie with the call of his girlfriend Rias Gremory, who was shaking her head a little in disappointment and awkwardness. The brunette blinked once, twice, then let out a small laugh, scratching the back of his head in embarrassment.

"Honestly, you have been spacing out quite a few times since last month." The heiress of Gremory sighed, then blinked at him a worried stare, placing both her hands on his shoulders on the sofa and looking at him deeply in the eyes. "Is there something wrong? You know you can always count of me."

"Y-Yeah! I'm okay! It's just... Damn Riser can't stop inviting me for a Rating Game, and with exams and all... But there's nothing you should be worried about, Rias!" He laughed, and forced himself to open a smile for her. For a second, she thought she saw a glimpse of it, but fortunately, Rias dismissed that small moment of weakness, and smiled at her boyfriend, happy to see his resolve for such problems despite his typical reaction to such. Little does she know, nothing that came out of his mouth was true.

But for her, everything was fine, even now that Grayfia was recovering from her previous state, and she was little by little regaining her typical persona, being stern and direct during duty, yet mellow and reliable when out of it, perhaps she became maybe _TOO_ mellow for some reason, but it was good. Whatever Issei did, it worked, and one day, she would come to be again. She will have her onee-san again, Millicas will get his mother back, the Gremory will have their maid back. Everything was good, everything was fine...

Everything was **fine**...

"Well, I think I better off and talk to Grayfia-san again. Maybe she'll... Know how to deal with those problems." Issei said, standing up from the couch and stretching himself. He opened another forced smile, and turned back to his girlfriend, who visibly pouted hearing the sudden news. She was upset that apparently now even Grayfia was hogging some precious time with her beloved pawn, but said nothing for two reasons: Whatever Issei was doing, if was working, and now that he was a High-class devil and Grayfia was his Queen, they needed some time to discuss things like Rating Games, specially since even high-classes have now the opportunity to fight him. Even with a pouty face, she nodded, and the red dragon emperor again flashed her an uneasy smile. "I'll be back for supper, don't worry! I'll be... I'll be back soon."

"Very well. Don't be late, it's a promise." Rias sighed, but then calm and gently smiled at her boyfriend, who tried his best to respond it back the same way. It's not like she wasn't used in sharing her dear Ise with other women, but thinking about Grayfia that way was both childish and a little awkward, fortunately she apparently had nothing to worry about, and at least Grayfia was returning back to normal. Before anything, however, she couldn't lose the opportunity to tease him a little with a bit of flesh, loosing the grip of her collar and another smile. "I'll be waiting for you, Ise. You promised me~."

"Yeah." Surprising for her, his reaction was a bit underwhelming than she expected. He wasn't that kind of pervert anymore, but overwhelming nonetheless. Maybe his mental state was worse than she anticipated, and her cousin and other champions were indeed starting to take a toll out of her beloved pawn, but, oh well, at least it gives her more reasons for a quick tease and get her pervert back at full health. Tonight indeed was going to be a fun night~...

Little did Rias notice, the moment Issei turned around, his expression was somber and dark...

The Gremory manor, the place His Beloved Rias used to live before the whole ordeal in that one year. He still can't believe all the things that have transpired ever since that date, and how far he had come for such. He had all the reasons to be happy, all the reasons to have a smile on his face, and yet, when he first stepped in front of that mansion, his entire world suddenly grew dark and lonely, and a clutch gripped his heart. Issei gulped hard, taking a deep sigh as everything and nothing would run into his mind. There he is again, and he'll do THAT again...

As always, he knocked at the door a few times, and the door opened to him, followed by the greetings of several butlers and maids of the Gremory house, lining all in front of him and Bowing like he was so kind of royalty. Well, to be honest, he kinda is now, but that is irrelevant now. Even with such polite and warm greeting, the brunette red dragon emperor couldn't stop the uneasy feeling his position inside that place was giving in, stepping inside only worsening it. As he walks inside the entrails of that place, he could only feel himself getting downer and downer. For the last weeks, that initially warm and welcoming place was the last place he wanted to be...

"Ah! Issei-oniisama! You're here!" Issei himself heard small steps coming closer, and for the first time since his arrival, he opened a small smile by seeing the small figure appearing by the horizon of the corridors. There he was, Millicas Gremory, Sirzechs' ultimate legacy in the world, brightly walking across the corridor with a contagious smile on his lips just to encounter his dear onii-sama. Once they met, the small redhead politely bowed, and received a cute pat on the head from the older male.

"Hi there, Millicas. Someone seems cheerful today." Issei, despite not having too much enthusiasm in his voice, said with a sigh and a smile to the little Gremory, who nodded at his words. Those little moments.

"Uh-huh! When this winter ends, I'll be allowed to be enter the Rating Game school, and Lewen everything I need to know about how to be a King." Millicas said, showcasing his newest uniform, and while Issei couldn't understand much, he was still happy to hear such good news. After a few seconds of silence, Millicas shared a stare with his future 'uncle-in-law' and blinked a few times in realization. "Oh, but you're here for mother, right? To talk about your next game."

"..." Issei had to bite his lips slightly so that he could maintain his happy facade for his dear 'nephew-in-law' and smile. Even he got over the loss of Sirzechs once Grayfia apparently came back from her previous state, and by the light he has on his eyes, his objective once he starts the Rating Game school was quite clear: he wanted to become just like Sirzechs and himself. Issei couldn't make himself break such illusion, so he did exactly how he did with Rias: just smiled. "Yes. I'm here for that. I hope I didn't keep her waiting. You know how Grayfia-san can be sometimes about schedule. Ahah... Ahahahah...!"

"But it is alright. If it's onii-sama, then I know you'll make Mother's Day even better." The younger Gremory innocently stated, and Issei again forced a smile upon his lips to the little guy.

Yes, ever since Issei started going to the Gremory manor and talking to the maid, Millicas also noted that his strict and stern, yet beloved mother was back, and she seems to be even mellower now after her 'talks' with the Red Dragon Emperor. He also thought that everything was okay, everything was fine. And just like Rias, when he bid his goodbye to his dear cousin-in-law, he didn't see the bitter expression on his face. Maybe it was for the best...

He had repeated the same walk so many times, he could remember the pattern of the Gremory manor like the palm of his own hand, and without asking any directions, he alone walked towards the room of the said Maid and Sirzechs' widow(?). Little by little, unconsciously the young man would slower and sluggish his own pace of his steps, getting closer and closer from the room the Gremory couple used to share, and now was only known as 'Grayfia's room'. A few seconds passed, and there he was again, at the door to her room, as always, the door being slightly open to shown that he could enter without any warnings. Issei sighed, and reached for the knob in order to slow and swiftly knocked it open with the knuckles of his hand. Inside of it, nothing else but darkness, the moonlight dimly tinting the room silver for Issei to have a general idea, but nothing else.

With the door already open, Issei could only look down at himself and take a deep breath, filled with uncertainties and doubt. Even so, here he is again, at the same place as before. Without warning, the high school student took a step inside and before anything else once in there, he turned around to close the door completely, and lock it down with a swift and quiet ***CLICK***. That was the signal, her signal. The moment that sound echoed inside the room, Issei felt himself embraced, as two soft plums landed on his back, and something warm shared itself with him. His usual response to that was underwhelming again.

"You're back... You're back for _me_." He heard from behind his back. Another heavy and guilty sigh escaped his lips as he turns around to see his lovely assailant. Despite the room not being illuminated by anything but the moonlight, he could see through the darkness the silver hair that was so loving and tenderly snuggling on him, rubbing on him in pure love and affection, yet his expression continue to be stuck like that. Another deep breath, another heavy sigh, and Issei turned around to face the figure who was now so attached to him.

"Yes, I'm Back... Grayfia-san." He called for her, and the maid of the house of the Gremory lifted her eyes to lock stares at him, softly smiling hearing him calling her. Looking deep into her crimson emptiness, he cursed under his breath for being so blind for it. Before anything else could be said, she tightened their embrace and came closer to kiss his lips, and Issei couldn't do anything but to reciprocate...

It has been months since the 666(Trihexa) incident, and after losing her beloved Sirzechs to the apocalyptically beast, Grayfia had entered a deep depression, which itself was bringing a rather gloomy atmosphere around the Gremory house, affecting those close to her as well like Millicas and Rias. Issei, being a good-natured goofball as only his, had Rias's blessing to try to cheer Grayfia up with his own comforting words, and after a series of events and a bit of alcohol from her, they almost have done the deed, Issei finding quite the unusual loophole to finally reach her(CAHAM!), and then help her with the issue at hand...

It was so weird and sudden, and he feared that once she would come back to herself, not only the problem would remain, but their 'ane and otoutou' relationship would suffer a drastic, if not downright abysmal, strain. Not to mention if she decides to put Rias of all people involved. Sure, his perverter mind thought another kind of development including both, but reason pierced him like an arrow for the worst hypothesis. Worst of all, he would be considered complete scum...

Alas... It didn't happen. In fact, quite the opposite happened: Grayfia had... Return to normal. Her strict and formal maid self remained the same during duty, if not a little mellower, but outside of it, he heard from both Millicas and Rias that she has indeed return, which filled the Red Dragon with both relief and joy. Even with his unorthodox method, he finally was able to return the smile of his dear ane, and even thought she could still love and miss Sirzechs, he can't blame her since he misses him too, such revelation would mean that she was in the right way for a good recovery, and a bright life and joy for surviving 666. For a while, the red dragon emperor too though that everything was fine...

However, as time passed, he began to notice something. Grayfia's visit to the Hyoudou residence became more and more frequent, and whenever she would stop by, she always tried to find ways to get closer to her 'little brother'. She would smile at him kindly, rest her head on him, snuggle dangerously close to his body and overall show even more affection to him than anyone else. She would also be the last to let go when the time would call for, and whenever she get the chance, she would clutch on him like a child and not let go.

Little by little, her smile began to fade its initial brightness, and as Issei would continue to look at her losing the shine in her eyes, only to look at his own reflection on her dull stare. It wasn't that she became neglectful of her duties and positions of the maid of Gremory and a mother, but while her sadness walked away, something new and mysterious bloomed inside of her, and its main target became the Red Dragon Emperor. She would ask for kisses, hug intimately his own 'brother in law' and request his company from time to time, fading a little every time that he would refuse. All the loneliness, pain, sorrow and depression became now love and affection, all for the sekiryuutei, and he didn't know why. It was only too late when he noticed what was wrong:

The moment Grayfia forgot about Sirzechs, everything else... Vanished as well.

Issei indeed underestimated the affection between the couple. He realized such too late, that the old Grayfia was gone now. The moment he ripped, even for a second, the love she has for Sirzechs in that intimate moment at the springs, he ripped her soul as well, the very event that was holding her entire personality together. The old Grayfia, who loved the redhead Lucifer, was gone. And in return, a new one was born. A new Grayfia... Who loved the Sekiryuutei with the entirety of her heart. A new Grayfia, who could again fall into the abyss of despair and sorrow. A new Grayfia... His heart told him to take care of, even if it means...

Even if it means...

Ever since that night, Issei started to engage himself into that for to the sole purpose of 'helping' the Gremory maid. It wasn't an obligation, it wasn't a way to take advantage of her, it wasn't his guilt over the fact that he took another Gremory for himself. It was just... His heart, telling him to take care of, to protect and love the broken Grayfia, even if it meant to threaten to cut all the ties he had build up until now. Sure, Rias was okay with the harem, but with her own sister-in-law... There was something very wrong about it, and he doesn't think she'll ever forgive him this time. Even so, every time they would kiss, embrace and entangled themselves on each other, such thoughts would become so vague, transparent, almost a ghost of what he truly felt for his redhead, even if for just a few hours, just those few hours...

What is love? Or pity? Honestly, he doesn't know anymore. Grayfia became his, and that is all there is to it. But that was enough, right? No more wine to forget about her husband, no more neglect as both a maid, a mother and a nee-san, no more sadness since she has him now, and he promised himself to never leave her so that darker days would return. He should be happy about it, right? Doing his 'usual stuff', helping someone with their problems, and will Rias and Millicas approval, it means he's done it again, right?

All those questions left unanswered, better yet, ignored, as he would embrace her and leave no areas unchecked in her body, even places he thought he'd never reach. A simple yet lingering, if just a little, reverie on the back of his head, while his body would pleasure and be pleasured by her. What Grayfia has become, she was slowly converting him as well. In those small moments of sex, of comfort, they would little by little forget their former lives and just share heat with one another. Right or wrong, good or bad, lack or excessive, it would all disappear as Grayfia would use her breasts, her lips, her tongue, her mouth, even her hair, hands, feet and, finally, her flower, to indulge herself with Issei. Sweat, semen, saliva, perfume, Issei was losing grasp of his own sanity while being intoxicated.

 _'I love Rias...'_

 _'I want to protect my friends...'_

 _'I want to be the harem King...'_

 _'I want to... Help... Grayfia-san...'_

Those thoughts were now simple memories, ghosts of what they used to be, as he pounds his hardest into Grayfia's most sacred place, seeing the hypnotic bounce of her breasts and her maddening calls for him, soon hushed by his lips of hers. All the nail marks on his back, his smell on the sheets, his echoing name from her mouth and, most importantly, the scorching hot memory he left in her deepest place, it all seemed like a sickly-sweet dream, that completely overshadowed all sorrow, all sadness, all remnants of pain from her... All the memories of her beloved Sirzechs from her.

Grayfia Lucifuge was now happier than she ever was since the incident...

And Hyoudou Issei wanted this to last...

Even if it means...

...

And it was over. They've lost track of time, and the moon in the sky was wordlessly indicating them how much it has passed. Now that he was his own person again instead of being merged into Grayfia's own skin, Issei could only pounder with himself, nude, on the edge of... Their bed. This was wrong, this was bad, but he continues to do this. It wasn't lust, it was... He doesn't know. But seeing Grayfia so happy, so satisfied, so back to herself makes him happy as well. There was no 'why', he simply knew what to do to make her happy, but in the end... Is he happy as well? Seeing her happy like this... Maybe... It was all worthy... Right?

 _Right_?

"Issei? Are you feeling well?" That sick sweet voice, calling him like a lover would. He didn't have the courage to turn around and face her, so he only lowers his head to look at the floor. A few seconds pass, and two soft mounts land on his naked back. What would get a comical reaction out of him, now was just more weight on him. Two hands reach for his shoulders, to them embrace his neck, so gently, like a maiden. "Issei... My Issei..."

"Grayfia-san..." He calls for her, and he hears her reaction as a cute giggle, followed by a kiss on the cheek. After that, nothing. Yes, she was happy, and that was all that matters... Right? He doesn't know, and from that moment on, he won't have to. It was just for a second, just for a second only, but his consciousness returns to him one last time, only to mutter his last words of regret: "I'm... Sorry."

"For what you're apologizing for?" She giggles, and in that moment, Issei is left speechless. Yeah, for what he's apologizing for? Grayfia was happy, Grayfia was his, and as long as she smiles and continues her life as a mother, a in-law and a maid, he's happy for her... Right? That is all he wants for her. That is what she deserves. Even if it means... She laughs again. "Issei..."

"Yeah...?"

 **"I love you."**

"..."

"..."

"Yeah."

And just like this, Grayfia Lucifuge is yet again...

 **Happy**.

* * *

 **Issei made Grayfia happy... But was it a happy ending? I hope you guys enjoyed this end chapter/epilogue and have a nice day. Nothing much to say, but I hope you had a great read and until we meet again.**

 **Greetings~.**


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